Dimethylformamide → HCID 71279316, compound

HRID 2171023Notes

Reaction equation

HRID 2171023 reaction equation
CS(O[C:6]1([CH2:9][O:10][C:11]2[C:16]([C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH2:19][CH2:20][C:21]4=[O:26])=[CH:15][CH:14]=[C:13]([O:27][CH3:28])[C:12]=2[O:29][CH3:30])[CH2:8][CH2:7]1)(=O)=O.[N-:31]=[N+:32]=[N-:33].[Na+].[CH3:35]N(C)C=O>>[N:31]([CH2:35][C:6]1([CH2:9][O:10][C:11]2[C:12]([O:29][CH3:30])=[C:13]([O:27][CH3:28])[CH:14]=[CH:15][C:16]=2[C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2[CH2:19][CH2:20][C:21]3=[O:26])[CH2:7][CH2:8]1)=[N+:32]=[N-:33]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 86677575HCID 86677575, compound

Product 1

HCID 71279316HCID 71279316, compound

Procedure

To a stirring solution of 1-((2,3-dimethoxy-6-(1-oxo-2,3-dihydro-1H-inden-4-yl)phenoxy)methyl)cyclopropyl methanesulfonate (3 g, 6.72 mmol) in dimethylformamide (20 mL), was added sodium azide (2.18 g, 33.63 mmol) and the resultant reaction mixture was stirred at RT for 16 h. The reaction mixture was quenched with ice water and extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-5% ethyl acetate in pet ether) to afforded 4-(2-((1-(azidomethyl)cyclopropyl)methoxy)-3,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one as a liquid.

Workup

  1. customthe resultant reaction mixture
  2. customThe reaction mixture was quenched with ice water
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined ethyl acetate layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography (silica gel, 0-5% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-389b450efeb6417f8023bfdd9f075915
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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